Synthesis and conformational analysis of new derivatives of 7-chloro-1,3-dihydro-5-phenyl-2h-1,4-benzodiazepine-2-one

TL;DR

This study synthesizes new derivatives of 1,4-benzodiazepine-2-ones via a green chemistry approach, confirming their structures and analyzing their conformations and stereochemistry using spectroscopic methods and computational modeling.

Contribution

It introduces a green synthesis method for new benzodiazepine derivatives and provides detailed conformational and stereochemical analysis.

Findings

Successful synthesis of new derivatives confirmed by spectroscopy

Identification of the most stable conformer through computational analysis

Investigation of diastereomeric forms using NMR spectroscopy

Abstract

1,4-benzodiazepine-2-ones and their derivatives are prominent structures in medicinal chemistry. These biomolecules have wide biological activities and posses therapeutic applications. In this works, we introduce new derivatives of 1,4-benzodiazepine-2-ones which are synthesized using michael addition reaction of 7-chloro- 1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-ones with fumaric esters that matches with green chemistry protocols. The structures of all products are confirmed by FT-IR, 1H-NMR, 13C-NMR and MASS spectroscopy. Since the stereochemistry of 1,4-benzo diazepine-2-ones is important, we study the most stable conformer of one of the products as a model for conformational analysis by hyper chem soft ware and semi empirical AM1 program. Also, using the 1H-NMR spectrum, we investigate the produced diastereomers of one of products as a model.